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Entry M0262    4.2.3.6    trichodiene synthase

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Step 05

Intramolecular electrophilic addition across the C10-C7 bond to form the five-membered ring.

GIF of Reaction Step M0262.stg05


Comment: The C10 carbocation is stabilised through long range electrostatic interactions with Asp100 and the pyrophosphate [1].



Mechanisms

Intramolecular Electrophilic Addition

Mechanism Components

Bond Formation
Bond Order Change
Intermediate Formation
Cyclisation

Amino acids involved in the reaction step.

Amino Acid Location of Function Activity Function
Tyr93 Side Chain spectator Polar Non-polar interaction
Electrostatic Stabiliser
Leu97 Side Chain spectator van der Waals interaction
Steric Role
Thr96 Side Chain spectator van der Waals interaction
Steric Role
Asp100 Side Chain spectator Metal Ligand
Electrostatic Stabiliser
Arg182 Side Chain spectator Electrostatic Stabiliser
Hydrogen Bond Donor
Lys232 Side Chain spectator Electrostatic Stabiliser
Hydrogen Bond Donor
Arg304 Side Chain spectator Electrostatic Stabiliser
Hydrogen Bond Donor
Tyr305 Side Chain spectator Electrostatic Stabiliser
Hydrogen Bond Donor

Metal Cofactors involved in Step 05

Metal Type Metal Identity Chain Activity Function
magnesium MG 701 B spectator Substrate Binding
Electrostatic Stabiliser
magnesium MG 702 B spectator Substrate Binding
Electrostatic Stabiliser
magnesium MG 703 B spectator Substrate Binding
Electrostatic Stabiliser

Reactive Centre

Bonds Formed Bonds Cleaved Bonds Changed in Order Atom Types Involved
C-C
None
The C-C bond changes from a double to single bond
C

View similar reactions in MACiE.


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